An expeditious route to eight- and nine-membered carbocycles based on a RCM-ring fragmentation strategy

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3209-3212

  Rodríguez, J Ramón ^a   Castedo, Luis ^a   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041849727     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0063959     Document Type: Article

References (39)

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35. Prepared in quantitative yield from commercially available 1,2-cyclohexanedione using standard silylation conditions. See the Supporting Information for details.
36. 1H NMR spectrum of the mixture by integration of characteristic signals of each isomer, which could be assigned owing to the feasibility of obtaining the trans isomer in pure form after subjecting the mixture to the metathesis reaction (see discussion that follows in the main text).
37. Bridge cleavage in related bicyclo[3.3.1]nonane systems has been based exclusively on Grob type of rearrangements: Hesse, M. Ring Enlargement in Organic Synthesis; VCH Publishers: Weinheim, 1991; p 199. See also ref 2b, p 5796.
38. 3N. DABCO and 2,6-ditertbutylpyridine failed to promote the epimerization.
39. Most of the trans isomer 3b was recovered during chromatography.